Synthesis, DFT and molecular docking of novel (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide as elastase inhibitor

• Published in: BMC chemistry 2023-08, Vol.17 (1), p.95-95, Article 95
• Main Authors: Mustafa, Muhammad Naeem, Channar, Pervaiz Ali, Ejaz, Syeda Abida, Afzal, Saira, Aziz, Mubashir, Shamim, Tahira, Saeed, Aamer, Alsfouk, Aisha A., Ujan, Rabail, Abbas, Qamar, Hökelek, Tuncer
• Format: Article
• Language: English
• Subjects: Aging; Analgesics; Anticonvulsants; Antiparasitic agents; Benzamide; Catalysis; Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Computer Aided Drug Design; Crystal structure; Crystallography; DFT studies; Elastase; Enzymes; Hirshfeld; Humanities; Hydrogen bonds; Inhibitors; Malaria; Molecular docking; Molecular dynamics; Molecular structure; Natural products; Pharmacy; Quinoline; Single crystals; Skin; Surface analysis (chemical); Toxicity; X ray analysis
• ISSN: 2661-801X; 2661-801X
• DOI: 10.1186/s13065-023-00985-4

A new compound, C 23 H 20 BrN 3 OS, containing a quinoline-based iminothiazoline with a thiazoline ring, was synthesized and its crystal and molecular structures were analyzed through single crystal X-ray analysis. The compound belongs to the triclinic system P  − 1 space group, with dimensions of a = 9.2304 (6) Å, b = 11.1780 (8) Å, c = 11.3006 (6) Å, α = 107.146 (5)°, β = 93.701 (5)°, γ = 110.435 (6)°, Z = 2 and V = 1025.61 (12) Å 3 . The crystal structure showed that C–H···N and C–H···O hydrogen bond linkages, forming infinite double chains along the b-axis direction, and enclosing R 2 2 (14) and R 2 2 (16) ring motifs. The Hirshfeld surface analysis revealed that H…H (44.1%) and H…C/C…H (15.3%) interactions made the most significant contribution. The newly synthesized (Z)-4-bromo-N-(4-butyl-3 (quinolin-3-yl)thiazol-2(3H)-ylidene)benzamide, in comparison to oleanolic acid, exhibited more strong potential against elastase with an inhibition value of 1.21 µM. Additionally, the derivative was evaluated using molecular docking and molecular dynamics simulation studies, which showed that the quinoline based iminothiazoline derivative has the potential to be a novel inhibitor of elastase enzyme. Both theoretical and experimental findings suggested that this compound could have a number of biological activities.